Perhaps you can set me straight on my premises again. To me, the joy of life comes from the challenges overcome. It is self-righteous of me to pretend that that perspective is shared by everyone. This point I grant.
That very point is why I should not be granted the power to decide for others how the ‘playing field’ should be ‘leveled.’ I might tilt it too far toward the challenges.

How can one design a democratic system that treats everyone fairly, and does not simply rob the few to benefit the many.
That is the political question.

How can one design a society, that punishes fraud and dishonesty, but allows for all types of speech? That is the economic question.

And how can one design a system, that is not elevated in importance above the parts that compose it. The minute the whole becomes greater than the sum of it’s parts, the system is misserving it’s parts.

You seem to have both an unduly skeptical view of the possible role of a democratically-elected government in preference-satisfaction, and an unduly naive view of unregulated capitalism. This isn’t economics, or even political theory — it’s theology.